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KMID : 0043320060290090721
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Archives of Pharmacal Research
2006 Volume.29 No. 9 p.721 ~ p.727
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Evaluation of Anticancer Activity of 4-Vinyl-1-Arylsulfonylimidazolidinones
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Kwak Son-Hyok
Bang Seong-Cheol
Seo Hyun-Hee
Shin Hye-Rim
Lee Ki-Cheol
Hoang Le Tuan Anh
Jung Sang-Hun
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Abstract
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To continue exploration of structure activity relationship of novel 1-(indoline-5-sulfonyl)-4-phenylimidazolidinones (1) reported as anticancer agent with broad spectrum, three 1-(arylsulfonyl)- 4-vinylimidazolidinones (2) were synthesized from methyl serinate (3) in 8 steps. Reaction of intermediate 2-phenoxycarbonylaminobut-3-enyl p-toluenesulfonate (10) with arylsulfonamide in the presence of potassium carbonate produced corresponding 2 and N-(4-vinyloxazolidin- 2-yl)arylsulfonamide 11 in approximately equal ratio. This reaction is believed to undergo through urea intermediate 16 as shown in scheme 3. 1-Arylsufonyl-4-vinylimidazolidinones 2 show much reduced activity against human colon carcinoma (Colo205), human chronic myelogenous leukemia (K562), and human ovarian adenocarcinoma (SK-OV-3) and compatible activity against human lung carcinoma (A549) compared to 1. Therefore phenyl at 4-position should be the optimum planar motif for the activity of 1.
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KEYWORD
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Synthesis and cytotoxicity of 1-arylsulfonyl-4-vinylimidazolidinones
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